I've not done business in Chile, but i have in Uruguay, which ranks about the same in terms of various transparency / economic freedom / gdp per capita as Chile. Everything he complains about is just the reality of living and working in latin america. Chile markets itself as being different, but it's not so different. Getting stuff done is hard, getting investment is hard, doing business is hard. There are lots of rules and red tape. It's just a part of the game.
The problem is that for nerds, the game is making stuff. The "doing business" part is what we have to go through in order to keep making stuff. And, as long as it is harder in Chile and other parts of Latin America, they will never come close to catching up to Europe, much less the US.